Abstract: 1. Methods have been developed for the synthesis of 2-butoxyethanethiol and bis(2-butoxyemyl) sulfide from butyl vinyl ether and hydrogen sulfide. 2. It has been shown that traces of oxygen (not more than 0.01% by weight), ascaridol, and the peroxide present in a concentrated solution of HCl in dioxane are catalysts for the addition of hydrogen sulfide to butyl vinyl ether contrary to Markovnikov's rule. 3. The free-radical nature of addition contrary to Markovnikov's rule is confirmed by the fact that it is retarded in presence of antioxidants. 4. It has been shown that a characteristic feature of the anomalous reaction is its inhibition by very small amounts of oxygen and peroxides, such as benzoyl peroxide, hydrogen peroxide, and the peroxide compounds formed during the storage of vinyl ethers. 5. It has been suggested that the inhibiting action of oxygen and peroxides is associated with the termination of chains resulting from the readily occurring secondary reaction in which radicals of the type RSCH2CHOR chain propagators) are oxidized.

Cite: Shostakovsky M.F. , Prilezhaeva E.N. , Shapiro E.S.
Synthesis of sulfur compounds by the aid of vinyl ethers and acetylene. Communication 7. Peculiarities of the reaction of addition, contrary to Markov Nikov's rule, of hydrogen sulfide to butyl vinyl ether
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1954. V.3. N2. P.235-243. DOI: 10.1007/bf01177619 OpenAlex

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W2062655849

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